What to ask before choosing a new CMS or a migration partner

A migration hides two decisions inside it. One is which platform to move to. The other is who does the moving. Both are easy to get wrong by asking about the wrong things, comparing feature lists and hourly rates instead of the handful of questions that actually predict how it will go. This is the list of questions worth asking before you commit to either, written so you can ask them without a technical background and know what a good answer sounds like.

For the broader question of choosing any software partner, our earlier pieces on common errors when picking a partner and red flags when hiring an agency cover ground this piece does not repeat. What follows is specific to a CMS and a migration.

Questions to ask about the CMS

Who owns and hosts it? Some platforms run only on the vendor’s infrastructure, which means your content and your ability to run the system depend on them continuing to offer it on terms you accept. Others you host yourself, on infrastructure you control. Neither is automatically right, but you should know which one you are choosing and what it implies. Ask directly: if we wanted to leave in three years, what would that take?

Can you get your content out? This is the portability question, and it separates a platform you own from one you rent. Content held as structured, exportable data is content you can move. Content locked inside a proprietary format is a future migration waiting to happen. Ask what your content looks like if you export it.

Can it deliver content to more than one place? If there is any chance you will need the same content in a website and an app, or across more than one site, ask whether the platform can serve content over an API to separate front ends. This is the headless question, and getting it right now avoids re-entering the same content in several systems later.

What is the editing experience for non-technical staff? The people who use the CMS daily are rarely in the room when it is chosen, and they are the ones who live with it. Ask to see the actual editing screen, not a marketing demo. If your team will fight it, the platform has failed at its main job whatever else it does well.

How is it priced as you grow? Watch for per-seat pricing that charges for every person who touches the content, because it attaches a fee to each new contributor, and contribution is exactly what you want the platform to encourage. Ask what the cost looks like at three times your current usage, not just today.

Is it actively maintained? A platform approaching its vendor end-of-support date is one you will be migrating off again sooner than you think. Check where a candidate stands before you commit, the same way you would check where your current one stands on our CMS end-of-life matrix.

Questions to ask the migration partner

Do you quote a fixed price against a fixed scope? A migration priced as an open-ended range against a loose brief means the real cost gets settled mid-project, when you have the least room to negotiate. A partner willing to fix the price against a written scope, with the out-of-scope items named, is a partner confident they understand the work. Ask for that, and treat reluctance as information.

Do you run discovery before you quote? In our experience perhaps one brief in ten arrives ready to quote against; the rest have gaps that only surface once someone looks properly. A partner who quotes instantly against your first description is quoting against those gaps, and the difference lands on you later. Ask what happens between “hello” and the number.

How do you define when something is done? The answer you want is that acceptance criteria are written alongside the scope, before the build, so “finished” is a question with an answer agreed in advance rather than one negotiated at the end. A vague answer here predicts a vague argument later.

Who owns the code, and what do I get at handover? The platform should be yours, on open technology, with documentation, so you can take it to another vendor at any time. Ask explicitly whether you own what they build and what the handover includes. A partner who keeps you dependent on them is selling you lock-in.

How do you handle redirects? This is a quiet test of whether they have done this before. Migrations lose traffic most often through URLs that changed without redirects, so a partner who brings this up before you do, and treats it as work that starts early, is showing you they know where the risk lives. We wrote about it in why we track redirects from day one.

Have you done this specific migration before? Moving off Sitecore is not moving off WordPress, and experience with the source system is worth a great deal. Ask what they have moved off, and off this platform in particular. Our migration guides are one way to see whether a partner actually understands the system you are leaving.

What the questions are really testing

Every question on this list can be asked without a technical background, and that is deliberate. Each one is a test of whether the platform and the partner have thought about the parts of a migration that go wrong, and whether they are being straight with you about the trade-offs. The answer worth trusting is specific, admits its limits, and does not ask you to take anything on faith.

If you want to run these questions past someone who will answer them plainly, including telling you when staying put is the better call, book a call and we will.